N,N'-bis<2-<(p-methoxybenzyl)thio>-2-methylpropyl>-2-aminobenzylamine | 158327-23-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis<2-<(p-methoxybenzyl)thio>-2-methylpropyl>-2-aminobenzylamine
• 英文别名: N-[2-[(4-methoxyphenyl)methylsulfanyl]-2-methylpropyl]-2-[[[2-[(4-methoxyphenyl)methylsulfanyl]-2-methylpropyl]amino]methyl]aniline
• CAS: 158327-23-2
• 化学式: C₃₁H₄₂N₂O₂S₂
• 分子量: 538.819
• InChiKey: ZQPZYRGDDFAFOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis<2-<(p-methoxybenzyl)thio>-2-methylpropyl>-2-aminobenzylamine 在 甲烷磺酸 、 苯甲醚 、 三氟乙酸 作用下， 反应 3.0h， 生成 N,N'-bis<2-mercapto-2-methylpropyl>-2-aminobenzylamine
  参考文献：
  名称：

  Technetium-99m N,N'-Bis(2-mercapto-2-methylpropyl)-2-aminobenzylamine: Technetium-99m Complexes of a Novel Bis(aminoethanethiol) Ligand

  摘要：

  A new N2S2 ligand system, N,N'-bis(2-mercapto-2-methylpropyl)-2-aminobenzylamine, U-BAT, 1, containing uneven amine groups (two amine groups with different pK(a) values) for complexing [(TcO)-O-V](3+), was prepared. The reaction of this novel ligand with [Tc-99m]pertechnetate, in the presence of stannous tartrate as the reducing agent, produces the neutral and lipid-soluble [Tc-99m](TcO)-O-V(U-BAT), TcS2C15H23N2O, 2. However, when the same reaction was carried out at a higher pH, 9-10, and with 30 min of heating (100 degrees C), a second neutral but more lipid-soluble complex, [Tc-99m](TcO)-O-V(OU-BAT), TcS2C15H21N2O, 3, was isolated. The X-ray crystallography data of the Tc-99 complexes show square pyramidal coordination with N2S2 as the base and the Tc=O in the apical position. Compound 3 can be derived from 2 by an oxidation of the ligand to form an imine. After iv injection into rats, the neutral and lipid-soluble technetium-99m complexes showed significant brain uptake, 1.54 and 1.07% dose/organ at 2 min for [Tc-99m](TcO)-O-V(U-BAT) and (TcO)-O-V(OU-BAT), respectively. The novel Tc chemistry of this new ligand system may provide a useful foundation for designing Tc complexes with a built-in redox mechanism.

  DOI：

  10.1021/jm00046a012
• 作为产物：
  描述：

  2-<(p-methoxybenzyl)thio>-2-methylpropionic acid 在 氯化亚砜 、 硼烷四氢呋喃络合物 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 4.0h， 生成 N,N'-bis<2-<(p-methoxybenzyl)thio>-2-methylpropyl>-2-aminobenzylamine
  参考文献：
  名称：

  Technetium-99m N,N'-Bis(2-mercapto-2-methylpropyl)-2-aminobenzylamine: Technetium-99m Complexes of a Novel Bis(aminoethanethiol) Ligand

  摘要：

  A new N2S2 ligand system, N,N'-bis(2-mercapto-2-methylpropyl)-2-aminobenzylamine, U-BAT, 1, containing uneven amine groups (two amine groups with different pK(a) values) for complexing [(TcO)-O-V](3+), was prepared. The reaction of this novel ligand with [Tc-99m]pertechnetate, in the presence of stannous tartrate as the reducing agent, produces the neutral and lipid-soluble [Tc-99m](TcO)-O-V(U-BAT), TcS2C15H23N2O, 2. However, when the same reaction was carried out at a higher pH, 9-10, and with 30 min of heating (100 degrees C), a second neutral but more lipid-soluble complex, [Tc-99m](TcO)-O-V(OU-BAT), TcS2C15H21N2O, 3, was isolated. The X-ray crystallography data of the Tc-99 complexes show square pyramidal coordination with N2S2 as the base and the Tc=O in the apical position. Compound 3 can be derived from 2 by an oxidation of the ligand to form an imine. After iv injection into rats, the neutral and lipid-soluble technetium-99m complexes showed significant brain uptake, 1.54 and 1.07% dose/organ at 2 min for [Tc-99m](TcO)-O-V(U-BAT) and (TcO)-O-V(OU-BAT), respectively. The novel Tc chemistry of this new ligand system may provide a useful foundation for designing Tc complexes with a built-in redox mechanism.

  DOI：

  10.1021/jm00046a012

文献信息

• Technetium-99m N,N'-Bis(2-mercapto-2-methylpropyl)-2-aminobenzylamine: Technetium-99m Complexes of a Novel Bis(aminoethanethiol) Ligand
  作者：Lynn C. Francesconi、Yun Y. Yang、Mei-Ping Kung、Xiao X. Zhang、Jeffrey J. Billings、Yu-Zhi Guo、Hank F. Kung

  DOI：10.1021/jm00046a012

  日期：1994.9

  A new N2S2 ligand system, N,N'-bis(2-mercapto-2-methylpropyl)-2-aminobenzylamine, U-BAT, 1, containing uneven amine groups (two amine groups with different pK(a) values) for complexing [(TcO)-O-V](3+), was prepared. The reaction of this novel ligand with [Tc-99m]pertechnetate, in the presence of stannous tartrate as the reducing agent, produces the neutral and lipid-soluble [Tc-99m](TcO)-O-V(U-BAT), TcS2C15H23N2O, 2. However, when the same reaction was carried out at a higher pH, 9-10, and with 30 min of heating (100 degrees C), a second neutral but more lipid-soluble complex, [Tc-99m](TcO)-O-V(OU-BAT), TcS2C15H21N2O, 3, was isolated. The X-ray crystallography data of the Tc-99 complexes show square pyramidal coordination with N2S2 as the base and the Tc=O in the apical position. Compound 3 can be derived from 2 by an oxidation of the ligand to form an imine. After iv injection into rats, the neutral and lipid-soluble technetium-99m complexes showed significant brain uptake, 1.54 and 1.07% dose/organ at 2 min for [Tc-99m](TcO)-O-V(U-BAT) and (TcO)-O-V(OU-BAT), respectively. The novel Tc chemistry of this new ligand system may provide a useful foundation for designing Tc complexes with a built-in redox mechanism.